RESUMEN
When conducting a photooxidation reaction, the key question is what is the best amount of photocatalyst to be used in the reaction? This work demonstrates a fast and simple method to calculate a reliable concentration of the photocatalyst that will ensure an efficient reaction. The determination is based on shifting the calculation away from the concentration of the compound to be oxidized to utilizing the limitations on the total light dose that can be delivered to the catalyst. These limitations are defined by the photoflow setup, specifically the channel height and the emission peak of the light source. This method was tested and shown to work well for three catalysts with different absorption properties through using LEDs with emission maxima close to the absorption maximum of each catalyst.
RESUMEN
The scale up of light-induced nickel-catalyzed Negishi reactions is reported herein, with output rates reaching multigram quantities per hour. This level of throughput is suitable to support preclinical medicinal chemistry programs in late lead optimization, where tens of grams to hundreds of grams of final product is needed. Adjusting reaction times and concentrations was critical in achieving this robust output. This example demonstrates how visible photochemistry and use of solid metal reagent can be used and how the progress of the reaction can be followed by in-line NMR monitoring.